Alkamins and process of producing same.



TED STATES TATE @FFIQE.

ALEX B. DAVIS, OF INDIANAPOLIS, INDIANA, ASSIGNOR TO THE ELI LILLY ANDCOMPANY, OF INDIANAPOLIS, INDIANA, A CORPORATION OF INDIANA.

ALKAMIN S AND PROCESS OF PRODUCING SAME.

No Drawing.

To all whom. it may concern Be it known that I, ALEX B. DAVIS, a citizenof the United States, residing at Indianapolis, Marion county, and Stateof Indiana, have invented and discovered certain new and usefulImprovements in Alkamins and Processes of Producing Same, of which thefollowing is a specification.

This invention relates to new alkamins derived from new halogen tertiaryalcohols. The alcohols are produced by the action of any organicmagnesium haloids on a new dihalogen ketone.

The process in general is as follows: Chlor-methyl-w-brom-propylcarbinol (produced by condensing ethylene bromid with epichlorhydrin) isoxidized by means of potassium dichromate to chlor-methyl-wbrom-propylketone. This is allowed to react with magnesium alkyl haloids whenchlor-tertiary carbinols are produced. These carbinols are condensedwith substituted amins when the new alkamins result. The salts of theiresters are valuable local anesthetics.

In detail, the process 'may be carried out as follows Step N 0. 1.'l 8parts by weight of magnesium metal in any suitable form, preferablyturnings or wire are placed in a vessel connected to a reflux condenserand 400 parts of absolute ether added. 218 parts of ethyl bromid are runin slowly through the condenser, a reaction sets in and the metaldissolves to form a compound of the formula:

When all the magnesium has dissolved there are run in slowly, throughthe condenser, 199 parts of chlor-methyl-w-brompropyl-ketone of theformula:

Speciflcation of Letters Patent.

Patented Aug. 1'7, 1915.

Application filed May 21, 1914. Serial No. 840,106.

lute acid, the ethereal layer which rises to the top separated, theether evaporated and the residue distilled in vacuum, when it boils atabout 98 under 10 mm. and has the constitution H2 CH3 The reactionprobably takes place as follows:

o ClCH2- -CH -CH -CH Br+BrMgCH CH +HC1= soda solution, the alkali beingadded in suf-' ficient quantity to liberate all the bases. This alkalinesolution is extracted several times with ether, the ethereal extractsunited, the ether and the excess dimethylamin evaporated and the residuedistilled in vacuum when it comes over as colorless liquid boiling atabout 96 under 15 mm. and has the constitution and which may be calleddimethyl-aminomethyl-ethyl-amyl-carbinol. Some other ethyl 'broinid inStep 1 an amin than dimethyl amin may be used in Step 2 and some otherhalo en ester than the resulting compound might then be represented bythe formula x CHr-N in which X and X are alkyl and hydrogen and Y, anymonovalent group capable of being introduced by means of its organicmagnesium haloids.

What I claim is 1. The process of producing alkamins by acting uponchlor-methyl-w-brom-propylkctone with alkyl magnesium haloids andcondensing the resulting tertiary alcohols with substituted amins.

2. The process of producing dimethylamino methyl-ethyl-amyl carbinol byacting upon chlor-methyl-W-brom-propyl ketone with ethyl magnesiumbromid and condensing the resulting tertiary alcohol with dimethyl amin.

3. Alkamins of the formula CHr-N i Y- -on in which X and X are membersof the group hydrogen and alkyl and Y a monovalent group capable ofbeing introduced by means of its organic magnesium haloids.

4:. An alkamin having the formula:-

In witness whereof, I have hereunto set my hand and seal atIndianapolis, Indiana, this sixth day of May, A. D. nineteen hundred andfourteen.

ALEX B. DAVIS. [L.S.]

Witnesses:

E. G. EBERHARDT, ARTHUR L. WALTERS.

